Mayr's Database of Reactivity Parameters

Carbanions in DMSO

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
anion of 2-phenylmalononitrile (in DMSO)
C9H5N2*
DMSO

N  Param.: 15.58

sN Param.: 1.00
***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
anion of 2-phenyl-2-(phenylsulfonyl)acetonitrile (in DMSO)
C14H10NO2S*
DMSO

N  Param.: 15.97

sN Param.: 0.72
***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
anion of (phenylmethylenedisulfonyl)dibenzene (in DMSO)
C19H15O4S2*
DMSO

N  Param.: 15.07

sN Param.: 0.79
***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
anion of 1,2,3-triphenylpropane-1,3-dione (in DMSO)
C21H15O2*
DMSO

N  Param.: 14.99

sN Param.: 0.83
***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
barbiturate anion (in DMSO)
C4H3N2O3*
DMSO

N  Param.: 15.59

sN Param.: 0.80
***J. Org. Chem. 2017, 82, 8476-8488
10.1021/acs.joc.7b01223
1,3-dimethylbarbiturate anion (in DMSO)
C6H7N2O3*
DMSO

N  Param.: 17.46

sN Param.: 0.72
***J. Org. Chem. 2017, 82, 8476-8488
10.1021/acs.joc.7b01223
2-thiobarbiturate anion (in DMSO)
C4H3N2O2S*
DMSO

N  Param.: 14.24

sN Param.: 0.82
***J. Org. Chem. 2017, 82, 8476-8488
10.1021/acs.joc.7b01223
1,3-diethyl-thiobarbiturate anion (in DMSO)
C8H11N2O2S*
DMSO

N  Param.: 14.90

sN Param.: 0.80
***J. Org. Chem. 2017, 82, 8476-8488
10.1021/acs.joc.7b01223
1-((diphenylmethylene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)
*
DMSO

N  Param.: 26.95

sN Param.: 0.52
***Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethan-1-ide (in DMSO)
C19H20NO2-*
DMSO

N  Param.: 27.77

sN Param.: 0.47
***Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
1-(benzylideneamino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)
*
DMSO

N  Param.: 29.10

sN Param.: 0.50
*Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
1-((4-chlorobenzylidene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)
*
DMSO

N  Param.: 29.02

sN Param.: 0.49
**Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
2-(benzylideneamino)-1-ethoxy-1-oxopropan-2-ide (in DMSO)
*
DMSO

N  Param.: 30.82

sN Param.: 0.41
**Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
cyano((diphenylmethylene)amino)methanide
*
DMSO

N  Param.: 29.50

sN Param.: 0.50
*Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO)
C11H10NO5-*
DMSO

N  Param.: 16.26

sN Param.: 0.83
***J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
enolate of 3-isochromanone (in DMSO)
C9H7O2-*
DMSO

N  Param.: 25.39

sN Param.: 0.54
***J. Org. Chem. 2024, 89, 6915-6928
10.1021/acs.joc.4c00277
enolate of 2-coumaranone (in DMSO)
C8H5O2-*
DMSO

N  Param.: 19.60

sN Param.: 0.75
***J. Org. Chem. 2024, 89, 6915-6928
10.1021/acs.joc.4c00277